Hollister
An older non-gated Windermere pocket with mature oaks and custom estates.
Live the MaxLife.
$1.1M
Median Price
$700K – $1.8M
130
Homes
$0–$60
Monthly HOA
1985
Established
Windermere Elementary (A-rated)
School Zone
Background
A brief history
Hollister was platted in the mid-1980s on land that had been part of the original Windermere citrus holdings — one of the older non-gated residential areas that predates the gated-community wave of the 1990s and 2000s. Roughly 130 custom lots were released, most built out between 1985 and 2000 as one-off customs. The neighborhood's light governance (minimal HOA, no architectural review on most lots) is the reason Hollister reads as architecturally varied today — 1980s two-story colonials, 1990s ranches, 2000s Mediterraneans, and a growing share of 2018+ farmhouse rebuilds share the same streets.
The feel
What it's like to live here
Hollister has the feel of an established Windermere neighborhood rather than a curated community — the kind of place where neighbors have lived for 20+ years and the tree canopy has grown in enough that summer afternoons stay cool under shade. Streets are lightly-trafficked two-lanes with no gate, no sidewalks on some blocks, and mature live-oak canopy throughout. Lots run 0.3 to 0.6 acre. The mix of long-tenured residents and newer renovation buyers gives the neighborhood a settled-but-refreshing character. Daily life orients around Windermere downtown (5 minutes) and the 429 for commute access.
The details
What to expect
Architecture & Lots
Architecturally mixed across four decades — 1980s two-story colonials, 1990s ranches, 2000s Mediterraneans, 2018+ farmhouse rebuilds. Main homes 2,600–4,800 square feet. Lots 0.3 to 0.6 acre. Mature live-oak canopy throughout.
Lifestyle & Amenities
Non-gated, no community pool or clubhouse. The tree canopy and neighborhood quiet are the amenities. Residents walk or bike to Windermere downtown, Fort Gatlin Park, and the chain of city parks. Weekend farmers' market in downtown Windermere is a local institution.
HOA Rules & Fees
Annual HOA $0–$720 (some blocks have small HOAs for road and common-area maintenance; others have none at all). No architectural review. Short-term rentals technically permitted but uncommon. Low-restriction neighborhood — one of the reasons buyers choose Hollister over a gated community.
Schools
Zoned for Windermere Elementary (A-rated), Gotha Middle, and Olympia High (A-rated). Windermere Prep (private) is 4 minutes.
Access & Commute
Four minutes to Windermere downtown, 10 minutes to the 429, 15 minutes to Disney, 20 minutes to Restaurant Row, 30 minutes to MCO.
Community
Amenities
- Mature live-oak canopy throughout
- Four minutes to Windermere downtown
- Non-gated with minimal HOA governance
- Architecturally varied custom-build stock
- Lower entry point for Windermere school zoning
Know Before You Buy
HOA rules worth knowing
- Annual HOA $0–$720 depending on block
- No architectural review
- Short-term rentals permitted but uncommon
- Non-gated community
Education
School assignments
- Windermere Elementary (A-rated)
- Gotha Middle School
- Olympia High School (A-rated)
- Windermere Prep (private)
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Current median trades in the $1M–$1.2M band. Unrenovated 1980s–1990s originals move $700K–$950K. Well-renovated homes run $1.1M–$1.5M. Recent custom rebuilds have closed $1.6M–$1.8M. Price-per-square-foot runs $250 for dated originals to $340 for renovated. Renovation status and lot size are the primary value drivers. Days-on-market has averaged 35–60 days.
Recent Work
Recent sales in Windermere
Representative closings across Windermere. Our Hollister off-market pipeline is larger than what's shown here.
No recent listings shown yet for Hollister. Join the VIP list to see upcoming inventory first.
Also Worth Seeing
Related communities
Windermere
Casabella
A small Tuscan-inspired enclave behind Windermere's quieter gate.
$2M – $4.5M · 50 homes
Explore Casabella →
Windermere
Metcalf Park
Windermere's original lakefront address — Lake Butler Boulevard.
$4M – $17.3M · 60 homes
Explore Metcalf Park →
Windermere
Parkside
A newer Windermere gated community with resort amenities and A-rated schools.
$850K – $1.8M · 320 homes
Explore Parkside →
Windermere
Tildens Grove
A guard-gated Windermere custom-estate community with resort amenities.
$1.4M – $4M · 175 homes
Explore Tildens Grove →
Want Hollister homes first?
Hand-picked Hollister matches — 48 hours before MLS. Two to three per month.
Information on this page is compiled from public records, MLS data, community associations, and broker observation. Price ranges, HOA fees, school assignments, and community amenities change — verify all details with MaxLife Realty and the relevant community association before making a purchase decision. Ryan Solberg, Broker, License #BK3354351. MaxLife Realty, 321.373.3536.